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Based on a visit during September 2002.

Painting of Portuguese ship, Sintra Palace.

The indispensable guidebook is Portugal, one of Dorling Kindersley's Travel Guides.
Portugal has coverted historic buildings, such as castles and monasteries, into hotels, called pousadas.  They are fantastic and memorable places to stay, often the most building in a particular location.  We stayed in the former monastery in …vora and in the castle of ”bidos.  This is the website describing all pousadas:  You also will find ways to contact them in any guidebook.
Another helpful website for travel all over Portugal is:
Portugal has many regional variations.  Don't do too much in one trip; don't try to see it all.  Below is the itinerary for our own trip in 2002:   Portugal Itinerary 2002.  And for a tried and true recommendation from a Spanish couple that visits Portugal often:  Extremadura (Spain) and Alentejo (Portugal).
We managed to visit the region of Alentejo.  Alentejo Region
We stayed in ”bidos.  ”bidos Area
We also had a visit to Lisbon -- far too short!  Lisbon
Don't miss the royal palace of Sintra.  Sintra
Cod -- "bacalhau" --  is the leading seafood and the national dish; it is often barbecued with olive oil.  You will find many other fish and seafood, as well.  There is more chicken than in Spain.  As all over the Iberian Peninsula, you will find ham on every menu.  The olives and the olive oil are superb and vary widely as we traveled around the country.  Everywhere you go, order cheese on the menu and you will get some excellent local cheeses, including sheep's cheese and "mountain" cheese.  See Portuguese Wines.  Wines were among the chief pleasures.  Wd didn't try the suckling pig, but many do:  Suckling Pig - Cascais
We find that small dictionaries are more useful than phrasebooks.  In Portugal, we used the dictionary most often while deciphering menus, but English versions sometimes are available.  Learn a few bsic phrases and you will get a warm response.  Assuming you don't speak Portuguese, start off with English or French.  Then, if that doesn't work, try Spanish.  The Spanish and the Portuguese can understand each other if they speak their own languages slowly.  There is absolutely no problem visiting Portugal if the only language you know is English.
See Literary and Musical Portugal, where the most important recommendation is to buy Paul Buck's book, Lisbon:  A Cultural and Literary Companion, in the Cities of the Imagination series (Interlink Books; New York 2002).  You will see beautiful tiles  -- everywhere.  Portuguese Tiles - Azulejos
Portugal is a country with small towns, and renting a car is advisable except for the Lisbon phase of your visit.  You will find, as we did, that there are almost no automatic transmission vehicles available from any major agency.  If you arrange one, I would not count on its actually being available when you arrive.  In our case, the two women in the group drove a stick shift, so the two men were confined to the back seat.  Also be warned that the Portuguese are known as the craziest drivers in Europe.  There is an unfolding superhighway and bridge system with modest tolls, and these are very lightly used.  They are a great way to get make tracks, but at the expense of local color.  Very important to US drivers:  stay in the right lane whenever possible.  No matter how fast you drive, someone coming out of nowhere will be on your tail if you are in the left lane.  Just stay out of their way.  Also be aware that there are many narrow and hilly roads, as well as small archways.  We often had to retract our side mirrors to get by other drivers and through streets.
As with every destination, consider safety issues:  Safety